First, I would have signed up for the Army whether my mom and then fiancee liked it or not. I've always wanted to learn how to fly helicopters and, frankly, I could have used the discipline.
As for my ex-wife, given what I know now, yes, I would have married her simply due to the fact I now have a great son from that marriage. I have a daughter as well but we don't speak. Oh, well. I would ended the marriage long before I did instead of prolonging the inevitable.